Know your audience. Some folks want wild and crazy, some want a bit lower key. Ensure that you’re planning for the groom’s interests and not for the script of some buddy comedy B-movie. Also, keep a sober party pooper in the group who can put a kibosh on activities before they get out of hand and cause problems.
Always have the number for a cab/Uber/Lyft/whatever handy to enable safe transport from whatever is planned to whatever impulsive whims strike the group after a few drinks.
We did a Jays game and then a beer hall with a big group including the groom to be's brother in law and co-workers. Afterwards a smaller group of us kept the night going. It was a good night and people appreciated being invited to the early stuff and the groom didn't feel awkward about having his co-workers see him getting messy later.
One thing to consider is the financial state of everyone being invited - you don't have to know everyone's income but don't put good friends/family members of the groom in a position where they might have to back out because it's too expensive. That's just as important if people also have to travel to the wedding.
Also, timing is key - if everyone is local you can do it a month or two before the wedding & potentially do a whole weekend (rented a cabin outside a small town for one). If you need to wait until the weekend of the wedding because there are people flying in or it's a destination wedding, then just try to make sure you're not doing it the night before a morning ceremony
@serotonein Yes, that's a very good point! The invite list has people from varying ages and stages of their careers so I'll be very conscious to try to be inclusive of everyone when planning activities.
For my brothers we went salmon fishing then to a White Sox game, but I have been to strip club bachelor parties in West Virginia and poker night Bachelor Parties and one where we just got super fucked up and road mini-bikes around a sub division. All were fun and varied quite a bit on cost. As long as you have a solid group of fellas you it will be a memorable night regardless.